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Viking Sky
Viking
Dec 14, 2028 - Dec 24, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$3,799pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 12, 2027 - Dec 27, 2027 (15 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • St John's, Antigua • Gustavia, St. Barts • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Charlestown, Nevis • Philipsburg, St. Maarten
Average Starting Price
$4,545pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$508pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Silver Shadow
Silversea
Jan 6, 2029 - Jan 16, 2029 (10 Nights)
San Juan del sur, Nicaragua • Rodney Bay, Saint Lucia • Grenada • Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Bequia Island, Saint Vincent • Roseau, Dominica • Little Bay, Montserrat • St. Kitts • San Juan del sur, Nicaragua
Average Starting Price
$5,400pp
Jim's Onboard Credit
Crystal Symphony
Crystal Cruises
Jan 7, 2029 - May 7, 2029 (120 Nights)
Melbourne, Australia • Portland, Australia • Penneshaw (Kangaroo Island), Australia • Adelaide, Australia • Adelaide, Australia • Esperance, Australia • Albany, Australia • Busselton, Australia • Perth (Fremantle), Australia • Perth (Fremantle), Australia • Komodo (Rinca), Indonesia • Benoa (Bali), Indonesia • Benoa (Bali), Indonesia • Waingapu, Sumba, Indonesia • Kupang, Indonesia • Darwin, Australia • Cairns (Yorkeys Knob), Australia • Cairns (Yorkeys Knob), Australia • Airlie Beach, Qld, Australia • Brisbane, Australia • Sydney, Australia • Wellington, New Zealand • Gisborne, New Zealand • Tauranga, New Zealand • Auckland, New Zealand • Auckland, New Zealand • Waitangi (Bay of Islands), New Zealand • Suva, Fiji • Apia, Samoa • International Dateline • Raiatea, French Polynesia • Bora Bora, French Polynesia • Moorea, French Polynesia • Moorea, French Polynesia • Papeete, French Polynesia • Huahine, French Polynesia • Rangiroa, French Polynesia • Fakarava, French Polynesia • Adamstown, Pitcairn Islands • Hanga Roa (Rapa Nui), Chile • Hanga Roa (Rapa Nui), Chile • Robinson Crusoe Island, Chile • Valparaíso, Chile • Puerto Montt, Chile • Castro, Chile • Chacabuco, Chile • Laguna San Rafael, Chile • Cruising the Chilean Fjords • Cruising the Chilean Fjords • Punta Arenas, Chile • Ushuaia, Argentina • Ushuaia, Argentina • Port Stanley, Falkland Islands • Puerto Madryn, Argentina • Puerto Madryn, Argentina • Punta del Este, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Montevideo, Uruguay • Montevideo, Uruguay • Balneario Camboriu, Brazil • Ilhabela, Brazil • Paraty, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Buzios, Brazil • Sao Salvador Da Bahia • Maceio, Brazil • Recife, Brazil • Santarem, Brazil • Boca de Valeria, Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Devil's Island, France • Bridgetown, Barbados • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico • Samana, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$74,100pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

49% OFF
MSC World Asia
MSC Cruises
Dec 19, 2027 - Dec 26, 2027 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$1,499pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

4% OFF
MSC World Europa
MSC Cruises
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$2,529pp
Jim's Onboard Credit
28% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Mar 14, 2028 - Mar 26, 2028 (12 Nights)
Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Grenada • Roseau, Dominica • St. Thomas • Miami
Average Starting Price
$7,699pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Dec 1, 2026 - Dec 22, 2026 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$3,214pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

33% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 4, 2028 - Feb 14, 2028 (10 Nights)
Bridgetown, Barbados • Willemstad, Curacao • Oranjestad, Aruba • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados
Average Starting Price
$6,099pp
Jim's Onboard Credit
Silver Spirit
Silversea
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Les Saintes, F.W.I. • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • St. Kitts • Roseau, Dominica • Bridgetown, Barbados
Average Starting Price
$4,600pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,769pp
Jim's Onboard Credit
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